N-bromobutanimide → 5-Bromo-2-(bromomethyl)benzonitrile

HRID 1921320Notes

Reaction equation

HRID 1921320 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][Br:11])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 129940045-Bromo-2-methylbenzonitrile

Product 1

HCID 442031405-Bromo-2-(bromomethyl)benzonitrileYield 38.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-bromo-2-methylbenzonitrile (5.0 g, 25.5 mmol), N-bromosuccinimide (4.54 g, 25.5 mmol), 2′,2′-azobis(2-methylpropionitrile) (0.05 g) and carbon tetrachloride (25 mL) is heated at reflux for 75 min. After cooling to room temperature, the solids are removed by filtration. The filtrate is concentrated and the residue purified by chromatography eluting with cyclohexane-20% ethyl acetate. Product containing fractions are combined and concentrated to afford 5-bromo-2-bromomethylbenzonitrile (2.69 g, 38%). LC/MS: MS showed no parent molecular ion peak; RT 3.52 min.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 75 min
  3. customthe solids are removed by filtration
  4. concentrationThe filtrate is concentrated
  5. customthe residue purified by chromatography
  6. washeluting with cyclohexane-20% ethyl acetate
  7. additionProduct containing fractions
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-88b50ee940064fe38590d9e5f5760b69
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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